zincophorin has been researched along with 3-hydroxybutanal* in 1 studies
1 other study(ies) available for zincophorin and 3-hydroxybutanal
| Article | Year |
|---|---|
A bidirectional approach to the synthesis of polypropionates: synthesis of C1-C13 fragment of zincophorin and related isomers.
The structure-activity study of a bioactive natural product containing polypropionate subunits requires that its stereoisomers also be evaluated. Therefore, a general approach to synthesize these motifs is necessary. We describe herein the synthesis of the C1-C13 polypropionate subunit of zincophorin and isomers thereof using a two-reaction sequence: an aldol reaction using a mixture of tetrasubstituted enoxysilanes and a hydrogen-transfer reaction, both under Lewis acid control. Selection of the appropriate Lewis acid dictates the stereochemical outcome of these reactions. From a tactical standpoint, this study shows how a polypropionate sequence can be read and constructed in two directions, either the east-west or the west-east approaches. The choice of the optimal route is influenced by the number of complexation sites that can interfere in the aldol step under bidentate Lewis acid control. Topics: Aldehydes; Chemistry Techniques, Synthetic; Hydrogen; Polymers; Propionates; Stereoisomerism | 2011 |